Playing Matchmaker
by elmo-x-takumi
Summary: Ash and company have noticed something between May and Drew. Heck, even Harley and May's mother have seen it! So now, Ash has called an expert on love to come and help them get May and Drew together! Contestshipping and AAML.
1. Let's Call the Expert

A/n: This is my first Pokemon fic! Anyways, this is a Contestship and Pokeship fic!

Summary: Ash and company have noticed something between May and Drew. Heck, even Harley and May's mother have seen it! So now, Ash has called an "expert" on love to come and help them get May and Drew together! Contestshipping and AAML.

I don't know where the real Kanto Pokemon Contests are, since the episdodes didn't air in the US yet. But I know that the contest in Saffron City is an accurate contest.

Disclaimer: I do not own Pokemon, or anything that has to do with it.

Hope you like it!

Story: Playing Matchmaker

Chapter 1: Let's Call the Expert

A group of two kids and two teens were staying in a room at the Pokemon Center. A boy with black hair was lying down on his bed, waiting with a small boy and an older boy for the bathroom door to open. Inside, the small boy's sister was taking one of her usual long showers that got the boy with the black hair, named Ash, impatient. His yellow mouse pokemon, Pikachu, continued to sleep on the bed next to him.

"Why does she take so long to use the bathroom?" Ash grunted. They had already taken showers and were dressed up, but Ash needed to use the bathroom again.

"That's what May usually does at home too." May's little brother, Max, replied.

"I guess all girls do that." The older boy, Brock, said.

May's ribbon case was on the desk in between the two bunk beds. Inside were beautiful ribbons that she won in Pokemon Contests. May, a very good coordinator, participated in the Grande Festival months ago, before Ash participated in the Hoenn League. Max looked at the case and remembered about Drew, May's rival. Drew was also at the Pokemon Center, to rest up before he gets back on his journey. This gave Max an idea.

"Hey guys, what do you think of May and Drew?" Max asked mischievously. This gained Brock and Ash's attention.

"Uh...they're rivals?" Ash asked. Max and Brock fell anime style.

"No. I mean...do you think that they could be more than friends?" Max asked again.

Brock smiled. "Well, we always see May coming to us with a rose in her hand and we always see Drew in the distance, so we know the roses always come from him."

"And he always shows off in front of May too." Ash said.

"If Drew and May were together, they could not only be more than friends, but help each other in contests!" Max said. "And, they could be one of the best coordinator couples in the world!"

"Not to mention Drew would stop showing off in front of _us_." Ash said. The three of them smiled.

"You thinking what I'm thinking?" Max asked and they nodded.

"Yeah." Brock replied. "But how're we going to get them together in the first place?"

A light bulb lit up in Ash's head. "We should get an expert to help us!"

Brock smiled and raised his hand. "That's me!"

Max then put Brock's hand down. "Yeah right. We need someone _else_. Someone we know. Someone...who has done this before and succeeded..."

"I have an idea of who." Ash said and got up from the bed, causing Pikachu to wake up.

"Pika?" Pikachu asked in confusion.

"Oh, good morning Pikachu." Ash greeted. "We're just going to call an old friend of ours before May gets out of the bathroom, which would probably be in 30 more minutes."

"Pi." Pikachu said and jumped onto Ash's shoulder. The four of them left their room and went to the main lobby where Nurse Joy was. She was sitting at her desk and using the computer. She looked up to see the four of them walk out of the rooms and look around the room for something.

"Good morning everyone!" Nurse Joy greeted. "What are you looking for?"

Ash sighed. "Nurse Joy, do you know where your phones are?"

Nurse Joy smiled and pointed at the line of phones. "There they are."

The four of them thanked her and went to one of the phones. Ash sat down on one of the seats in front of the phones and dialed a number. Brock, Pikachu and Max didn't know who he was calling, but waited for a response from the person Ash called. The screen lit up and a girl with orange hair appeared.

"Wow! Hey you guys! Long time no see!" The girl greeted.

"Hey Misty." Ash greeted back. "I was calling to ask if you can help us play matchmaker."

Misty raised an eyebrow. "Matchmaker? Who are we going to get together?"

"May and Drew." Max replied. Misty looked at them in confusion.

"Who's Drew?" Misty asked.

"Drew is a coordinator like May. They're rivals, but we know there's something between them. He always gives her roses but he always shows off in front of us, and especially May." Max explained.

Misty thought a bit and smiled. "Well, you're just in luck! They just built a few Pokemon Contests near Cerulean City, Viridian City, Cinnabar Island, Saffron City and Pallet Town. And guess what! The contest in Cerulean City is for partners only! Hmm...is Drew with you?" Brock nodded. "Then it's settled then. Once you need to do what you need to do, get May and Drew to come with you back to Pallet Town. Then we can go to the contest there, and get May and Drew to pair up for the contest in Cerulean City. I'll come along, since my sisters are back in the gym again."

"Alright! Thanks Misty!" Ash exclaimed and Misty smiled as they hung up. As soon as Ash got up from his seat, the four of them began cheering and jumping. Pikachu needed to hop down from Ash's shoulder so he wouldn't get dizzy. May had finished taking a shower and walked into the lobby to see them cheering.

"Uh, guys?" May started, startling them. "What're you guys doing?"

"We have good news!" Ash replied. "There are Pokemon Contests back at home!"

May began to smile. "Wow! Really?"

"Yeah!" Brock replied. "We should all go to Pallet Town and meet up with everyone and you can participate in some of the contests!"

Max thought of something and became as happy as Ash and Brock were. "Yeah! We should get Drew to come along!"

As soon as May heard that, she froze and widened her eyes. This was the reaction that Max was waiting for. Many thoughts appeared in May's head. Should they let him come along? He might win everything, but he'll be there with her. If he didn't come, then not only will May be able to win most of the contests, but be without Drew's presence. Ash and Brock noticed that she was thinking hard and was slightly blushing. May blinked and looked up at them.

"I guess we should invite him to come huh?" May replied and noticed Drew come out of his room and walk into the lobby. He went up to Nurse Joy and saw her get up and go to the back to get his pokemon.

"Why don't you go ask him?" Ash asked May. May froze again, but slightly nodded nervously. She walked over to Drew, who didn't notice her walking up to him. As soon as he felt a presence come towards him, he turned around to see May.

"H-hey Drew." May greeted.

"Hey May. I see you've brought your friends along too." Drew greeted.

"Oh, yeah. Well, my friends just told us that there are Pokemon Contests in Ash and Brock's home region and we're wondering if you'd want to come along." May asked, clearly.

There was silence between them. Drew was deep in thoughts and looked up at May. "Okay. Sure. When are we going?"

Ash, Brock, Max and Pikachu walked towards Drew. "Tomorrow at 12. There's a plane leaving nearby for Pallet Town, which is my hometown and where a Pokemon Contest is. We can all sleep over at my house."

Drew smiled and flipped his hair. "Okay. Hope I don't get as many fans over there than here. I had someone stalk me on the way here."

May became a bit angry at the fact that Drew was showing off again. "We'll meet back in the lobby tomorrow morning at 11:30."

"Alright. See you later." Drew said as he received his pokemon from Nurse Joy. "I'll be training for the pokemon contests for now. Bye May. Hope you don't lose as much as you did in Hoenn."

Drew left the Pokemon Center and went to a certain spot outside. He released his Masquerain and Roselia to train.

May was growling but slightly blushing. "Grr...can you believe the nerve of that guy? For once I just want him to shut up! I hate him!"

Nurse Joy heard all that she said. "May, are you sure that you hate him? Like they say, the one you hate is the one you love."

May began to blush more than she already did. "No! I don't love him!" This caused Ash, Brock, Pikachu and Max to laugh. "Stop laughing at me!"

Nurse Joy then handed everyone their pokemon. "Well, you should practice for the contests now too. You never know how hard it'll be to win a ribbon in Kanto."

"Yeah I guess I should." May replied and went back to the room to get her belongings. She went outside and noticed Drew working really hard.

"Razor Leaf Roselia!" Drew exclaimed. "And use Quick Attack to dodge them Masquerain!"

Roselia put its two roses together and sharp leaves shot out of them, elegantly shooting themselves with a little sparkle at Masquerain's direction. Masquerain dodged all of the sharp leaves using its Quick Attack. Roselia stopped its Razor Leaf and Roselia and Masquerain smiled.

"Good job you two!" Drew exclaimed. May just continued to watch from afar and sighed.

"When am I ever going to tell you?" May asked in a small voice that only she could hear.

A/n: There goes the first chapter! Will Ash and the others succeed at getting Drew and May together? Or will Drew continue to be just a rival to May? Next in Chapter 2!

Chapter 2: Plane Ride to Kanto

Read and review!


	2. Plane Ride to Kanto

A/n: Thanks to those who reviewed and added this story to their favorites or alerts! But I'm sorry to say that the next time this fic will be updated is probably in 1 to 2 weeks. This has nothing to do with a writer's block so don't worry! It's just that school will be hard on me as usual and like my previous stories, it will take a while to get another chapter updated.

Sorry I updated in one month X( I couldn't find any free time to update all of my stories, since I had too much homework, my computer needed to get rebooted, I was sick, and because my birthday was this month! And to be honest, I finished this chapter two weeks ago! Whoops! Another reason was because I couldn't decide whether or not I should update this story with the other stories. The last time I updated, I updated 2 stories and created 3 stories, including this one. Before, I was so confused about which story I haven't updated, so I made a little WordPad to record my story stats XD I didn't want to have this story to be held back with the other stories so I decided to update the stories as soon as I get their chapters completed! Yay!

I didn't feel like replying to you guys' reviews personally, so I'll answer them right here:  
**Ri2** - Thanks! And I would also thank you for the accurate places where Pokemon Contests are held! I appreciate it!  
**pokebunny** - Thanks for the review! And I'll try to update this story as soon as I can.  
**GiGi - MistyShrine** - Thanks for the review!  
**neogirl7900** - Lol, thank you for the review!  
**Nick Johnson** - Uh, alright! This will be a bit long though. You can find the answers to some of your questions if you read the summary and the first chapter, but it's alright. And it's spoiler free too! Here are the answers: 1. This fic is about how Ash, Misty, Brock and Max have noticed a relationship forming between May and Drew. By reading the first chapter, you will see that Ash and Misty have made a plan to get them together by bringing Drew with them to Kanto so they could battle together. But there will be some Pokeshippy moments starting to form later in the story. 2. Hm, I don't really know the _date _of this story, but this does take place after the Hoenn League but before the group goes to Kanto. The story first starts off in Hoenn, but I didn't say where exactly. So I'll just say that they're in Slateport City, where I added an airport, and since a Pokemon Contest is nearby. 3. In this fic, I'll say that Ash is 14, Brock is 16, Misty is 14, May is 11, Drew is 12, and Max is 10. 4. Hm, this is a hard question. I think that there are only a few characters, such as OC trainers and coordinators and some characters such as Misty's sisters, Brock's family, Ash's family, May and Max's parents, Harley, the main characters' pokemon, a few other people from the Orange Islands, maybe someone like Rudy, my character from my Emerald game (Yuri, and that's a name! It means lily! Not like that Yaoi or Yuri thing :( ) and some other people. I'm really not sure, since I still need to figure out who all of the main and minor characters are. 5. Some of the characters will try and get in the way of the Pokeship and Contestship. Again, I'm not sure of who the characters are, so I'm sorry to say that I can't really answer this question. Okay, there you have it! And thanks for reviewing and asking me those questions!  
**Matt and T.K.** - Thanks!  
**Zen the sexy demon** - Thanks to you too!  
**gamer** - Thanks to you as well!  
**ssx Kaori fan** - Lol, thanks for the review! Yeah, don't worry! There _will _be Pokeshipping in the later chapters, just have patience - you'll need it. It'll take me a while to update chapters :(

Okay, now onto the story!

Chapter 2: Plane Ride to Kanto

Drew continued to practice with Roselia and Masquerain and May secretly watched from afar. Ash, Max and Brock had left to buy some supplies before they left so they could buy whatever they wanted the next day. May blinked and sighed.

"Well, I should train my pokemon too." She thought and walked away from Drew and on the other side of the Pokemon Center. She grabbed all but one of her used Pokeballs and pressed the buttons in the middle. The balls grew twice their size and May threw them in front of her. "Come on out everyone!"

The balls then opened, releasing May's pokemon. One was like a butterfly, a small dinosaur with a bulb on its back, a pink cat, and a tall chicken. The butterfly, Beautifly, came out of its Pokeball with sparkle all around it. It cried and smiled. The small dinosaur, Bulbasaur, hopped in happiness and cried as well. The pink cat, Skitty, began to chase its tail in a small circle, happily. And the tall chicken, Combusken, simply cried and smiled.

"We're going to Kanto with Drew, so we'll have to try and beat him in a contest!" May told them happily and her pokemon smiled. "He is training right now, so I guess we should too, right?"

Her pokemon nodded. "Alright! Ash and the others didn't tell me if the contests were different, so I guess we'll just practice on our moves and combos okay?" May asked and her pokemon cried happily. "Okay, you first Skitty! Use your Blizzard and use Assist afterwards!"

Skitty jumped in front and opened its mouth, shooting out a beam of ice. It aimed it on the ground creating a huge spiky ice sculpture. Still in the air, it opened its mouth again, and another beam shot out of it. It took a while to generate the attack as Skitty stored energy from the sun. It unleashed a powerful shiny Solarbeam at the ice sculpture it created, causing it to shatter into very tiny pieces, making them glitter in the air.

"Alright! Good job Skitty!" May exclaimed. "Your turn Beautifly!"

Beautifly stepped up. May continued to train all of her pokemon until it turned dark. She yawned and smiled at her pokemon. "Well, it's getting late you guys. Time for you to get some rest before we leave tomorrow!" She exclaimed and held out all of her pokeballs. Her pokemon cried happily and a beam of red light showed on them and turning the pokemon red as well. Soon, the light began withdrawing back to the pokeball, taking the pokemon with it. As soon as all of her pokemon were in their appropriate pokeballs, May sighed and smiled again. Suddenly, she heard a noise from behind her. It wasn't the kind of noise that would scare anyone, but a congratulatory kind of noise. May turned around to see Drew clapping a few feet behind her.

"Good job on training your pokemon today May." Drew said and held out a red rose. He held it in front of her and May took it, while slightly blushing. "You'll need all the help you can get when we're in Kanto. It was a good idea to practice."

May smiled. "Th-thanks Drew. How long were you watching?"

Drew flipped his green hair. "When I heard you tell your Skitty to use its Blizzard attack and Assist. I don't really know why but Roselia seemed interested to watch you two. So we decided to stop training and watch another coordinator practice with their pokemon. Hopefully you won't lose in a contest when you get the wrong attack for your Skitty's Assist." He said boldly.

May looked at Drew with anger. "What is that supposed to mean? Can you for once stop talking as if you know everything? I _will_ win a contest in Kanto whether you like it or not! There _will _be a time when you'll lose to _me_ you know!" She exclaimed. He simply shrugged in response.

"Whatever May." He replied. "I'm still better than you. Goodnight May. See you tomorrow."

He turned and entered the Pokemon Center. May sighed and noticed that Max, Ash and Brock had returned with paper bags filled with an assortment of berries, potions, full heals, a few pokeballs, some human food, and pokefood. Pikachu was on Ash's head, holding a ketchup bottle and licking the ketchup as if it was pokefood. They looked at May with confusion.

"Were you just talking to Drew?" Max asked her.

"Yeah. He was complimenting me on a job well done on training my pokemon." May replied, showing them the rose and yawned. "Can we just go to sleep now so we can go shopping in the morning and leave?"

"Wait, we have to tell Mom and Dad first." Max told her.

The group entered the Pokemon Center and May gave Nurse Joy her pokemon. The group ate their dinner and immediately went to the phone booth and called the Petalburg Gym. Caroline and Norman, Max and May's parents, approved and sent over some extra supplies and food from home that Max and May loved.

As soon as the call finished, the group went to bed. They took off their accessories and put it on the desk where May's ribbon case was in the morning. May slept on the bottom bunk and Max slept on the top bunk. Brock slept on the other top bunk and Pikachu and Ash slept on the other bottom bunk.

May looked out the window from her bed. She sighed. 'I can't believe we're going to Kanto with _Drew_.' She thought. 'Maybe this won't be as bad as I thought. Can't wait for tomorrow and catch some new pokemon for the contests!' She smiled and went to sleep, dreaming of what would happen the next day. The alarm clock on the desk read 11:26 PM.

_THE NEXT DAY_

The group woke to a start by the buzzing sounds from the alarm clock. May looked up to see that it was 7 AM. She yawned drowsily and walked into the bathroom. The guys did the same and took turns going into the bathroom. When May finished, she walked into the lobby where Nurse Joy sat at her desk. She looked up at her and smiled.

"Good morning May!" Nurse Joy greeted. "Today is the day when you'll be going to Kanto am I right?"

May nodded. "Yep! And I'm so excited to catch some pokemon for the Pokemon Contests too!"

Nurse Joy smiled. "Speaking of pokemon, your pokemon are ready for you to be picked up! I'll go get them." She got up from her seat and went to the backroom where the pokemon were being rested. May looked around the Pokemon Center for the last time in Hoenn as she waited. Nurse Joy came back a few minutes later with a tray holding 5 pokeballs.

"Here you go!" Nurse Joy exclaimed and handed them to May. "I hope you have a good time while you're still here May."

"Thank you!" May replied and walked back to their room, where Ash, Pikachu, Max and Brock were already ready.

"Let's go eat some breakfast before we go shopping okay?" Brock asked and they all nodded. The group made sure they had all of their belongings with them in their backpacks and left the room. The group came back to the lobby where Nurse Joy sat. Drew was already getting his pokemon and waited for Nurse Joy to get his pokeballs. He turned around and noticed May and the others standing near him.

"Are you getting ready Drew?" Ash asked.

Drew flipped his hair. "I've been ready. I'm just going to do some shopping for a while before we leave."

Nurse Joy had returned from the backroom and handed back Drew's pokemon as well. "Here you are Dr--" Nurse Joy wasn't able to finish her sentence due to someone holding one of her hands. She looked up to see Brock looking lovey-dovey at her. Nurse Joy sweatdropped. 'Here we go again...' She thought, unimpressed.

"Why hello my star from the heavens!" Brock exclaimed. "I just want to say that I will be leaving soon and I want to know if you'll miss me -- OW OW OW!"

Max began pulling Brock's ear in order for him to get away from Nurse Joy. "Oh don't worry Brock. She won't miss you, she'll be glad you're not here!"

May, Ash, Drew and Nurse Joy sweatdropped. Then, May turned to Drew. "We were just going to get some breakfast. Do you want to come with us?"

Drew shook his head. "No, I ate breakfast an hour ago. I'll go and check up with my pokemon for now and then we'll go shopping for supplies. I want them to be the best that they can be for the Pokemon Contests. Robert may have beat me, but at least he probably won't be in Kanto with us. Besides, I know someone will beat _you_ at least."

Just as May began to build rage, he had exited the Pokemon Center to check up on his pokemon. She sighed and turned to the group. "Let's go get some breakfast shall we?"

The group ate breakfast and went shopping for whatever they wanted before they went to Kanto. May bought a pokedoll that her pokemon could play with, some of her own accessories and clothing, some pokemon needs and blended some pokeblocks for her pokemon, especially her _Purple Surprise_ for Munchlax. Ash bought Pikachu the ball that he wanted so he could play with it. Max bought an updated book filled with pokemon details and where to catch them, since he was going to get his first pokemon very soon. Brock bought two books; one for breeding and the other for helping him be a better trainer like Ash. Brock was going to substitute his father, Flint, at the Pewter City gym for a day while they were going to Cerulean City. The group was then walking by a small jewelry shop. A light bulb lit up in Ash's head and he and Pikachu ran inside, buying a charm bracelet. The group except for Pikachu and Ash knew the reason why he bought the bracelet.

May looked at the time to see that it was almost 11:30. "Hey guys, we should be heading back to the Pokemon Center by now. I bet Drew's already there waiting for us!" She exclaimed.

"Hmm...and why do _you_ care if Drew is waiting or not?" Max asked, slyly. May looked at him and slightly blushed.

"W-well, he _is _coming with us to Kanto you know!" May replied, nervously. Max simply shrugged in response and Ash, Pikachu and Brock smiled. The group began to walk back to the Pokemon Center. As they reached it, they started to find where Drew was.

"Pika!" Pikachu exclaimed as he looked in one direction. The others looked where Pikachu was looking to see Drew at the phone booth, receiving lots of items from whoever he was talking too. The group shrugged and began to tip-toe over to where he was to catch a glimpse of who he was talking to.

As soon as they got closer, May noticed that he was talking to a girl on the other side. "Now I want you to take care okay? We've sent you everything you needed." The girl with brown long hair with light green highlights, who was about Drew's age, said. "I'll miss you Drew."

"...I'll miss you too." Drew replied and hung up. May felt rage building in her mind, just hearing Drew tell a girl that he'll miss her. He took his backpack and stuffed whatever the girl sent him via phone. He picked up a brown wrapped package and began to open it. Drew widened his eyes as he fully took off the wrapping paper. It was a rectangle medium sized blue box of some sort, but Ash and the others couldn't tell what it was.

Just then, Drew felt a presence behind him. He turned around to see May, Ash, Pikachu, Brock and Max looking at him while trying to hide behind the couch in the lobby near the phone booths. "How long have you guys been over there?" Drew asked and sweatdropped.

"Long enough to see you talking with your girlfriend!" May exclaimed, and Drew's eyebrows rose.

"That wasn't my girlfriend May. That was my _sister_." Drew replied, unimpressed. May looked around at Ash and the others and blushed. Drew began to laugh. "You actually thought that she was my girlfriend?"

May and the others nodded and Drew chuckled. "Well there you have it. I don't have a girlfriend. Can we just go now?"

They nodded and smiled. Drew admitted that he _didn't_ have a girlfriend! That meant that May had a chance! Max, Ash, Brock and Pikachu continued to smile as they left the Pokemon Center with May leading the boys to the airport. They had already bought the tickets for all five of them, so all they needed to do was give their tickets to the female flight attendant.

"WHOAH!" Brock exclaimed and attempted to go and talk to the female flight attendant face to face, but Max held him back.

"Now's not a good time Brock!" Max exclaimed as he continued to hold him back while they got onto the plane.

The plane was very crowded and there were hardly any seats available for them. Max and Brock sat next to each other, while Ash sat in the available seat in front of them with Pikachu on his lap. May and Drew looked around to see only two seats in the plane left. They were side by side and were next to the window. 'No way! I am not going to sit next to Drew!' May exclaimed in her head as Drew sat in the seat closest to the window. Seeing that that seat was the only seat available, she sighed and sat next to him. Ash, Brock, Pikachu and Max smiled and high fived each other.

"Please sit in your seats while the plane is in motion." The speaker in the plane said. "This flight will take about 4 hours to get to Pallet Town in the Kanto Region, so please sit tight."

'_Four hours_?' Drew and May thought simultaneously. '_With May/Drew?'_

"Alright! This is going to be great!" Max whispered to them. "Four hours with each other! Wonder how May's feeling?"

'This is a nightmare!' May thought as the plane began to move. The plane began to fly off the tracks and into the air towards Kanto.

END OF CHAPTER 2

A/n: There goes Chapter 2! Hope you guys like it! What happens on the plane to Kanto? Will May survive being next to Drew for four whole hours? Will _Drew_ survive being next to May for that long? Will they argue or be more like friends? What awaits them when they arrive at Pallet Town? Read chapter 3!

Chapter 3: Bonding With Rivals

Read and review please!


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